Microsoft’s CEO is still haunted by staying silent in a meeting with Bill Gates—years later, his boss Steve Ballmer taught him how to speak up

Satya Nadella spent more than two decades climbing the ladder at Microsoft before becoming CEO in 2014. But looking back, the billionaire recently admitted that he once failed to speak up when he believed the company was making the wrong call—and is still haunted by the memory today. Nadella recalled a meeting in around 2008-2009 called by then-chairman Bill Gates to review a potential acquisition involving a team working on parallel data warehousing. Nadella, who was leading Microsoft's search engine team at the time, thought the deal made little sense. "I looked at it, [and thought], it is completely architecturally stupid in that time to go buy that," Nadella said on an episode of the Confession with Ali Partovi podcast released this week.